Another method to form a peptide bond involves a two-step process: [1] Conversion of a
Chapter 28, Problem 28.67(choose chapter or problem)
Another method to form a peptide bond involves a two-step process: [1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. [2] Reaction of the p-nitrophenyl ester with an amino acid ester. C OH Boc N H C O R1 H C O NO2 Boc N H C O R1 H C Boc p-nitrophenyl ester N H C O R1 H 2N CH C OR' O H R2 [1] [2] + O NO2 C H N C OR' O H R2 new amide bond a. Why does a p-nitrophenyl ester activate the carboxy group of the fi rst amino acid to amide formation? b. Would a p-methoxyphenyl ester perform the same function? Why or why not? C O OCH3 Boc N H C O R1 H p-methoxyphenyl ester
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